NYC Exclusive West Village Speakeasy and Gangsters Tour

Step into the Prohibition era and explore the West Village, NYC's original sanctuary for rebels and outlaws. Discover how the tangled streets of "Little Bohemia" became the ultimate hideout for 1920s underground culture and hidden speakeasies. This tour blends legendary landmarks with the neighborhood's darker side. You’ll see the Hess Triangle, Jimmy Kelly’s, the iconic Friends exterior, and the Stonewall Inn, while hearing ghost stories of the famous "Thinnest House." The highlight is a curated circuit of three lore-steeped drinking stops: the Art Deco Zinc Bar, exclusive entry to "The 86" (the mob-linked former Chumley’s where "getting 86’d" was coined), and The Garret, a secret speakeasy hidden above a burger joint. A rare glimpse into NYC’s most captivating history!

1. 1

   Stop 1

   30 min

   Pass by the historic facade of NYU's Furman Hall, the former site of Edgar Allan Poe's home. Travelers will hear tales of Greenwich Village's darker history, learning how the eerie streets that once inspired 'The Raven' eventually became the stomping grounds for New York's most infamous 1920s gangsters and hidden speakeasies

2. 2

   Washington Square Park

   15 min

   Stroll past historic Washington Square Park and discover the hidden, darker side of this famous landmark. Hear tales of how the surrounding tree-lined streets and brownstones provided the perfect cover for the city's most elusive gangsters, bootleggers, and underground drinking dens during the height of the Roaring Twenties.

3. 3

   The Stonewall Inn

   20 min

   Walk past the iconic Stonewall Inn. Though famous for the 1969 uprising, this site also harbors deep ties to New York's organized crime history. Discover how the Mafia ran this hidden 'bottle bar,' bribing local precincts and running a shadowy establishment that echoed the underground, mob-run drinking dens of the Roaring Twenties

4. 4

   Stop 4

   15 min

   Don't blink or you'll miss the Hess Triangle, a mosaic tile marking the smallest plot of private land in NYC. Pass by this quirky landmark and hear the story of one man's ultimate act of defiance against the city government—a stubborn, anti-authority attitude that perfectly mirrors the Prohibition-era outlaws you'll learn about on this tour

5. 5

   Stop 5

   15 min

   Pause outside the heavy, unmarked door of 86 Bedford Street to discover the secrets of a true 1920s underground speakeasy. You'll learn how illicit patrons sneaked inside to avoid police raids, and hear the local legend of how this very address may have birthed the popular bartender slang to '86' an unruly customer.

6. 6

   The Garret

   20 min

   Discover how the West Village keeps its rebellious history alive as you pass by The Garret. Hidden away on the second floor above a very unexpected storefront, this contemporary speakeasy serves as a perfect example of how the secretive, 'hidden-in-plain-sight' culture of the Prohibition mobsters continues to inspire New York's modern nightlife

• Wheelchair accessible
• Infants and small children can ride in a pram or stroller
• Service animals allowed
• Public transportation options are available nearby
• Suitable for all physical fitness levels
• Persons under the age of 21

For a full refund, cancel at least 24 hours before the scheduled departure time.